In 1967, 16 men from Anguilla - a forgotten island in the Caribbean - set sail aboard The Rambler to make the night-time journey to St. Kitts, where they intended to carry out a coup d'etat and install a new government. Set against the turbulent background of world politics in the 60s and loosely based on the historical facts of the Anguilla Revolution, The Night of the Rambler tells their story. It touches upon universal topics of freedom and self-determination with humour and sensibility, creating an alternate reality informed by real life.